Water → HCID 57933027, compound

HRID 1432726Notes

Reaction equation

Br[C:2]1[S:3][C:4]([C:8]2[N:12]3[N:13]=[C:14]([CH3:22])[CH:15]=[C:16]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:11]3=[N:10][C:9]=2[CH3:23])=[C:5]([Br:7])[N:6]=1.[Li]CCCC.O>C1COCC1>[Br:7][C:5]1[N:6]=[CH:2][S:3][C:4]=1[C:8]1[N:12]2[N:13]=[C:14]([CH3:22])[CH:15]=[C:16]([CH:17]([CH2:18][CH3:19])[CH2:20][CH3:21])[C:11]2=[N:10][C:9]=1[CH3:23]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 3-(2,4-dibromo-thiazol-5-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (4.86 g, 10.6 mmol) in THF (150 mL) under N2 atmosphere at −78° C., BuLi (6.63 mL 1.6 M in hexane, 10.6 mmol) is added dropwise for a period of 10 minutes. The mixture is stirred at −78° C. for 30 minutes. Water is added, and the mixture is extracted with Et2O (3×100 mL), dried over MgSO4 and concentrated in vacuo. Crude product is purified by flash chromatography on silica gel (eluent hexane:EtOAc 5:1) to give 3.28 g of the title compound (Yield: 82%). ESIMS: m/z 379, 381 [M+H]+.

Workup

extractionthe mixture is extracted with Et2O (3×100 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customCrude product is purified by flash chromatography on silica gel (eluent hexane:EtOAc 5:1)

Sources & evidence

ORD record: ord-1f70def6c40b4e16a51e2ee55ac0ee2f
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612067B2

Reaction notes

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